Winthrop Walking Trails and Maps

68 Reviews

Looking for the best Walking trails around Winthrop?

Find the top rated walking trails in Winthrop, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

Maine’s Eastern Trail will eventually extend from Casco Bay in South Portland to the Piscataqua River in Kittery, partially along the former Eastern Railroad. Three off-road segments of the trail are...

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

A stunning gateway to Maine's capital city, the Kennebec River Rail-Trail follows the railroad right-of-way that once connected Portland to Augusta. The trail parallels the inactive railroad tracks,...

The quiet Kennebec Valley Trail (a.k.a. Anson to Bingham Trail) boasts surprising claims to fame: the 14.6-mile trail traces the river and Indian path taken in 1775 by Benedict Arnold, on orders from...

Named for the railroad line it parallels, the Mountain Division Trail will one day span 52 miles between Fryeburg and Portland. Two sections of the trail are currently open. A 6-mile segment between...

The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...

The paved Papermill Trail follows the Sabattus River from Mill Street south to its confluence with the Androscoggin River and beyond. At its northern end, the trail parallels Mill Street then Upland...

The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...

The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...

The paved Papermill Trail follows the Sabattus River from Mill Street south to its confluence with the Androscoggin River and beyond. At its northern end, the trail parallels Mill Street then Upland...

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

Maine’s Eastern Trail will eventually extend from Casco Bay in South Portland to the Piscataqua River in Kittery, partially along the former Eastern Railroad. Three off-road segments of the trail are...

Named for the railroad line it parallels, the Mountain Division Trail will one day span 52 miles between Fryeburg and Portland. Two sections of the trail are currently open. A 6-mile segment between...

The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...

A stunning gateway to Maine's capital city, the Kennebec River Rail-Trail follows the railroad right-of-way that once connected Portland to Augusta. The trail parallels the inactive railroad tracks,...

The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

Named for the railroad line it parallels, the Mountain Division Trail will one day span 52 miles between Fryeburg and Portland. Two sections of the trail are currently open. A 6-mile segment between...

The paved Papermill Trail follows the Sabattus River from Mill Street south to its confluence with the Androscoggin River and beyond. At its northern end, the trail parallels Mill Street then Upland...

Maine’s Eastern Trail will eventually extend from Casco Bay in South Portland to the Piscataqua River in Kittery, partially along the former Eastern Railroad. Three off-road segments of the trail are...

The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...

A stunning gateway to Maine's capital city, the Kennebec River Rail-Trail follows the railroad right-of-way that once connected Portland to Augusta. The trail parallels the inactive railroad tracks,...

The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...

The quiet Kennebec Valley Trail (a.k.a. Anson to Bingham Trail) boasts surprising claims to fame: the 14.6-mile trail traces the river and Indian path taken in 1775 by Benedict Arnold, on orders from...

The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

The quiet Kennebec Valley Trail (a.k.a. Anson to Bingham Trail) boasts surprising claims to fame: the 14.6-mile trail traces the river and Indian path taken in 1775 by Benedict Arnold, on orders from...

The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...

The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

The paved Papermill Trail follows the Sabattus River from Mill Street south to its confluence with the Androscoggin River and beyond. At its northern end, the trail parallels Mill Street then Upland...

Maine’s Eastern Trail will eventually extend from Casco Bay in South Portland to the Piscataqua River in Kittery, partially along the former Eastern Railroad. Three off-road segments of the trail are...

Named for the railroad line it parallels, the Mountain Division Trail will one day span 52 miles between Fryeburg and Portland. Two sections of the trail are currently open. A 6-mile segment between...

The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

A stunning gateway to Maine's capital city, the Kennebec River Rail-Trail follows the railroad right-of-way that once connected Portland to Augusta. The trail parallels the inactive railroad tracks,...

Recent Trail Reviews

Kennebec River Rail Trail

Great First Ride

My husband and I just both got bikes and were at a family outing the day before in Augusta and decided to try out the trail. It was a beautiful trail and a great first ride. We will definitely be back!

Kennebec Valley Trail

Bingham area section

Visiting Maine in August we found no place to rent bikes within 80 miles of the Trail. We decided to hike the section from Bingham south as we like free flowing rivers, not lakes behind dams. First issue was the Bingham Goodrich Rd trailhead. It is in the woods and out of sight from US 201 or houses. We chose to park at a more publicly visible location at a Supermarket across from North Country Rivers Outfitters where the Trail crosses a corner of the Outfitters property. We did get permission from the Supermarket and recommend parking here, not the Goodrich Rd. trailhead.

Second, the main issue for us was the Trail. This included the lack of views of this section of the river being obscured by Summer vegetation, the condition of the trail with muddy potholes and lack of a gravel surface and the permitted use of the Trail by ATV’s. The ATV drivers were respectful of hikers and slowed for us, but the vehicles were still noisy and created dust. We terminated the hike early and had ice cream at Here’s the Scoop in Bingham, sitting quietly on the bank of the Kennebec.

Headed south on US 201 to Arnolds Landing where the trail crosses the Kennebec. The trail is on the river bank and would have provided better water views had we hiked this section. Had to leave, as it is a slow drive from I-95. In summary, the Bingham area portion of the Trail would rank as our worst RTT experience from Maine to Virginia. We would not return even for ice cream on the river bank.

Mountain Division Trail

x country skiing

So 15 degree weather does not stop us!
Started at otter pond and skied to Gambo Field.
Beautiful blue sky and crisp air. Maine the way it should be. Met a few snowmobiles and only a few other brave walkers. I love this trail and feel so blessed to be able to walk out the door and have this great place to play.

Belfast Rail Trail on the Passagassawaukeag

five stars is right!

a wonderful thing about this trail is that it is handicapped accessible from the outer High Street parking lot in particular. The stone dust surface is impervious to wheels and motor driven and otherwise propelled wheel chairs are very easy to use on the trail.

That said... the trail is a wonder. There are three parking area access points. 1. downtown/intown where it intersects the Armistice Bridge walking bridge and Harbor Walk, 2. Upper Bridge (on High Street) and 3. out at the The Brooks Preservation railroad yard, station, and museum.

Belfast Rail Trail on the Passagassawaukeag

Excellent trail with great views

The trail is beautifully groomed and hugs the Passagassawakeag river for over 2 miles. We started at the north end (13 Oak Hill Road) of the trail by the rail yard. The parking lot was packed when we got there as the excursion train was getting ready to leave. They have rides Saturdays and Sundays at 1 PM. The trains travel north from the parking lot and the trail goes south. The trail surface is perfect for walking and biking. It is treelined and has many small bridges that carry you over creeks. It took us 45 minutes of walking to get to the southern end at the intersection of Pierce St. and Front St. in Belfast. There is now a trailhead with a small parking lot at the southern end (not listed in the description). The trail connects there to the Belfast Harbor Walk which is an awesome urban trail through Belfast harbor and Front Street shipyard with a long pedestrian bridge across the Passagassawakeag.

Eastern Trail

Shady, and no hills

We rode as a pair from the Kennebunk Elementary School, which is at the southern end of the trail - marked as "mile 28" northward.(It's about .2 miles from the parking lot) Aside from crossing over Rt. 95 just at the base of the trail, from then on it was flat, perhaps a slight grade up while heading north. The surface is sand, and fine gravel. There are a few benches along the trail. Very scenic trail with dense woods and streams. It's an easy trail, with no hills to climb, if that's what you're looking for. I recommend it.

Mountain Division Trail

Not much to see

Having ridden bike paths all over New England, I've enjoyed many wonderful experiences towing my toddler in his trailer. My wife and I rode this southern section starting in Standish, and we were generally disappointed. There is little to see, aside from a field and a bridge over a pond. The path had a few potholes and places where a safety fence were falling down. It also doesn't really lead you anywhere interesting, like a place to eat or a town to explore. We wouldn't return to ride this again.

Eastern Trail

Kennebunk to Biddeford

We parked at Kennebunk Elementary School, cycled to Biddeford, and had a great breakfast at All Day Breakfast Two, just a couple of blocks from the trailhead, before returning to Kennebunk. The trail is in excellent condition. We used our regular road bikes with no trouble. A highlight was the sight of a fox sauntering down the trail!

Mountain Division Trail

Beware ore Deer Flies

I wasn't sure if dogs were welcome on the Fryeburg end of the trail, but I brought her with me. Unfortunately the DEER FLIES were horrible! It looked like such a nice walk. I will try again another day, with bug spray!

Papermill Trail

Lisbon Paved Gem

June 9, 2016; This paved trail is a gem for those who live in the surrounding Lisbon area. There are multiple lots to park easily, as the guide suggests. It was my first rail trail, since I have started to take riding more seriously. Great trail, new pavement, beautiful landscape and river, very pleasant folks and no obstacles on any part of the trail. I was able to carve out 8.3 miles (biked the trail twice and added a couple investigative turnouts). I would highly recommend it to others and will do it again, if I find myself in that area. Happy trails!

Mountain Division Trail

Nice trail

It's a nice trail and you have access all around the trail. The trail leads to a camp so it's a big trail to drive on but there are all these small trails on the side that you can walk down that lead all over the place.My favorite side trail is the train tracks and it leads to the the lake and the bridge.I have been there lots of times only been on the side trails one time and have never made it to the end of the drive part but it is still lots of fun.